That is a (generic) timeout while sending mail
BTW do you really want the world to see you Kindle account address? (folk usually replace that with something like <obscured> ) so the log message is not destroyed, but...

Ok another update - i downgraded to version 0.8.17 and changed my outgoing email addy to my Yahoo address and it seems to work now. I guess i will just stick with this version since i know it works. Or it does at the moment. Thanks for everyones help so far, and if you have any more recommendations for me let me know and i will try them! =)

That is a (generic) timeout while sending mail
BTW do you really want the world to see you Kindle account address? (folk usually replace that with something like <obscured> ) so the log message is not destroyed, but...

Um well if they are not on my account as able to send anything to my Kindle i dont know what they could possibly use it for, but i have never really thought about that. Thanks for letting me know for future reference though

Ok another update - i downgraded to version 0.8.17 and changed my outgoing email addy to my Yahoo address and it seems to work now. I guess i will just stick with this version since i know it works. Or it does at the moment. Thanks for everyones help so far, and if you have any more recommendations for me let me know and i will try them! =)

I don't normally use that feature, but in testing with 9.6 I learned that the 'test' button results in sort of useful (ya gotta read geek) error messages

You may have more than one fault in you configuration (I had 2.5)
(I use my ISP's mail server)
1) the username (and domain)
2) The correct password for the account (I had an old one from a long ago test)
3) The sent from must be a full email address

and last but not least: The to address must be correct (and with Amazon, you must enter the senders email address into you manage my Kindle.

Yeah all that had been correct when i was using my main email address so i dont know what the problem is but it seems to be working now with my yahoo address and the downgraded version i'm using. I dont know how to test the configuration of calibre to make sure there are no issues.

Off topic question but gonna ask, is there a way to make a second library on Calibre, cause mine is used for 2 different people's books and i dont really want my books mixed in with their's and so if i could make a seperate library for their's i would like to. But if not thats ok too.

Yeah all that had been correct when i was using my main email address so i dont know what the problem is but it seems to be working now with my yahoo address and the downgraded version i'm using. I dont know how to test the configuration of calibre to make sure there are no issues.

Off topic question but gonna ask, is there a way to make a second library on Calibre, cause mine is used for 2 different people's books and i dont really want my books mixed in with their's and so if i could make a seperate library for their's i would like to. But if not thats ok too.